Alyssa Mastromonaco worked for Barack Obama for almost a decade, long before his run for president. From the then-senator's early days in Congress to his years in the Oval Office, she made Hope and Change happen through blood, sweat, tears, and lots of briefing binders.
But for every historic occasion-meeting the queen at Buckingham Palace, bursting in on secret climate talks, or nailing a campaign speech in a hailstorm-there were dozens of less-than-perfect moments when it was up to Alyssa to save the day. Like the time she learned the hard way that there aren't nearly enough bathrooms at the Vatican.
Full of hilarious, never-before-told stories, WHO THOUGHT THIS WAS A GOOD IDEA? is an intimate portrait of a president, a book about how to get stuff done, and the story of how one woman challenged, again and again, what a "White House official" is supposed to look like. Here Alyssa shares the strategies that made her successful in politics and beyond, including the importance of confidence, the value of not being a jerk, and why ultimately everything comes down to hard work (and always carrying a spare tampon).

This isn’t a run of the mill political memoir. This is the story of what can and will go wrong. It is the story of friendships forged in stress and sleep deprivation. It is finding out how to stand up for yourself and your ideas when you are young and female in a job that has always been dominated by older men.

I loved a story that she discussed early in the book. She was in charge of scheduling Barack Obama’s time. During the 2008 campaign there was bad weather forecasted. She decided to have him go ahead with a live outdoor event in spite of the weather. It ended up being worse than expected and he was getting hit in the face with sleet through the whole speech.

We watched (in horror) as the event drew to a close, and Obama reached his hand to Reggie. As we were turning off the TV, my phone rang.

“Alyssa, it’s Obama.”

“Hi!” I said, with my head down on the desk, girding myself for the inevitable and deserved. “The event looked AWESOME! You heard John McCain canceled all of his events, right? He looked like a total old man!”

“Alyssa, where are you right now?”

I was not sure where he was going with this, but I knew it was somewhere bad. “My desk,” I replied cautiously.

“Must be nice.”

Click

She doesn’t shy away from discussing the very personal aspects of the job. One of her proudest moments was getting tampon dispensers in the bathrooms of the White House. Most of the people working there had been men and post-menopausal women so it hadn’t been thought a priority. She also discusses her IBS and the problems that causes in a job where there is a lot of stress and questionable food choices.

She talks about the questions she gets about not having children. She was working all the time during her twenties and thirties. She didn’t marry until she was 37. People ask her now if she is sorry that she didn’t have children. I love that she is unapologetic about not being sorry. She proudly proclaims her status as child-free and having cats instead.

Her job encompassed everything from setting up the schedule for the President to coordinating federal emergency response to Hurricane Sandy and the Haitian earthquake. Where do you go from there? She talks about how hard it is to leave the White House and decide what to do with your life.

One of the hardest parts of reading this book was remembering what it was like once upon a time. You know, back when the U.S. Presidency wasn’t a total embarrassment. I liked hearing about the personal side of Obama. He introduced her to Mindy Kaling at an event because he knew she had been reading her book. He got Bruce Springsteen to call her from a campaign event because she had to stay at the White House after setting up the concert and she was a huge fan. He called her a year after she quit working at the White House because he heard her cat died that day. (Everyone knew her cat. He was famous. She had a conversation about his health problems with George W. Bush on the way to Nelson Mandela’s funeral.)

This is a short book and a quick read. I read it in one sitting. I’d recommend this book to everyone who wants to know what it is really like to work in the White House.

I just have two criticisms. First, she uses a lot of nicknames for people. It can be a bit hard to remember who these people actually are when she is using nicknames long after introducing them by their full names. Second, I feel like she underplays her accomplishments a bit. She talks about women being conditioned to not stand up and present their ideas and it seems like she is still doing that some here. If a man wrote a book about doing this job, I feel like it would be a lot more about “Look at me! I was awesome!” I wouldn’t necessarily like that book as much as I liked this one but what she did was pretty amazing and sometimes that gets lost.

About Alyssa Mastromonaco

Alyssa Mende Mastromonaco is the Chief Operating Officer of Vice Media. She is also a contributing editor at Marie Claire magazine. She previously served as White House Deputy Chief of Staff for Operations in the administration of President Barack Obama from 2011 to 2014.She was the youngest woman to hold that position. Mastromonaco had worked for Obama since 2005 when he was on the United States Senate as his Director of Scheduling.